Page last updated: 2024-11-12

2-ethylestradiol sulfamate

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

2-ethyloestradiol-bis-sulfamate: structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID11583423
CHEMBL ID425287
SCHEMBL ID3690812
MeSH IDM0464503

Synonyms (20)

Synonym
bdbm50200941
2-ethylestradiol 3,17-o,o-bis-sulfamate
CHEMBL425287 ,
2-ete2bismate
stx 243
2-ethyloestradiol-bis-sulfamate
2-ethylestradiol-3,17-o,o-bis-sulfamate
stx-243
(9beta,13alpha,14beta,17alpha)-2-ethylestra-1(10),2,4-triene-3,17-diyl disulfamate
WZB ,
2-ebm
SCHEMBL3690812
3OIK
2X7T
estra-1,3,5(10)-triene-3,17-diol, 2-ethyl-, disulfamate, (17beta)-
556813-12-8
'2-ethylestradiol 3,17-o,o-bis-sulfamate'
Q27467377
[(8r,9s,13s,14s,17s)-2-ethyl-13-methyl-3-sulfamoyloxy-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl] sulfamate
PD180444

Research Excerpts

Bioavailability

ExcerptReferenceRelevance
" We have previously shown that a number of sulphamoylated analogues of 2-MeOE2 possess enhanced potency and bioavailability with respect to 2-MeOE2."( Inhibition of MDA-MB-231 cell cycle progression and cell proliferation by C-2-substituted oestradiol mono- and bis-3-O-sulphamates.
Leese, MP; Potter, BV; Purohit, A; Raobaikady, B; Reed, MJ, 2005
)
0.33
" The compound was orally bioavailable (31% after a single 10 mg kg(-1) dose) and resistant to metabolism."( The in vivo properties of STX243: a potent angiogenesis inhibitor in breast cancer.
Chander, SK; Foster, PA; Jhalli, R; Leese, MP; Newman, SP; Parsons, MF; Potter, BV; Purohit, A; Reed, MJ, 2008
)
0.35

Dosage Studied

ExcerptRelevanceReference
" The potential of 4 as an orally dosed anti-tumor agent is confirmed using breast and prostate cancer xenografts."( 3,17-disubstituted 2-alkylestra-1,3,5(10)-trien-3-ol derivatives: synthesis, in vitro and in vivo anticancer activity.
Bubert, C; Ferrandis, E; Ho, YT; Kasprzyk, PG; Leese, MP; Mahon, MF; Newman, SP; Potter, BV; Purohit, A; Reed, MJ; Regis-Lydi, S, 2007
)
0.34
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (6)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, CARBONIC ANHYDRASE 2Homo sapiens (human)Ki0.23200.23200.23200.2320AID977610
Chain A, CARBONIC ANHYDRASE 2Homo sapiens (human)Ki0.23200.23200.23200.2320AID977610
Chain A, CARBONIC ANHYDRASE 2Homo sapiens (human)Ki0.23200.23200.23200.2320AID977610
Carbonic anhydrase 2Homo sapiens (human)IC50 (µMol)0.29000.00021.10608.3000AID47745
Carbonic anhydrase 2Homo sapiens (human)Ki1.32600.00000.72369.9200AID1249520; AID1624852
Steryl-sulfataseHomo sapiens (human)IC50 (µMol)1.00000.00010.40717.6000AID275881
Carbonic anhydrase 9Homo sapiens (human)Ki0.25000.00010.78749.9000AID1624851
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (18)

Processvia Protein(s)Taxonomy
morphogenesis of an epitheliumCarbonic anhydrase 2Homo sapiens (human)
positive regulation of synaptic transmission, GABAergicCarbonic anhydrase 2Homo sapiens (human)
positive regulation of cellular pH reductionCarbonic anhydrase 2Homo sapiens (human)
angiotensin-activated signaling pathwayCarbonic anhydrase 2Homo sapiens (human)
regulation of monoatomic anion transportCarbonic anhydrase 2Homo sapiens (human)
secretionCarbonic anhydrase 2Homo sapiens (human)
regulation of intracellular pHCarbonic anhydrase 2Homo sapiens (human)
neuron cellular homeostasisCarbonic anhydrase 2Homo sapiens (human)
positive regulation of dipeptide transmembrane transportCarbonic anhydrase 2Homo sapiens (human)
regulation of chloride transportCarbonic anhydrase 2Homo sapiens (human)
carbon dioxide transportCarbonic anhydrase 2Homo sapiens (human)
one-carbon metabolic processCarbonic anhydrase 2Homo sapiens (human)
steroid catabolic processSteryl-sulfataseHomo sapiens (human)
female pregnancySteryl-sulfataseHomo sapiens (human)
epidermis developmentSteryl-sulfataseHomo sapiens (human)
response to hypoxiaCarbonic anhydrase 9Homo sapiens (human)
morphogenesis of an epitheliumCarbonic anhydrase 9Homo sapiens (human)
response to xenobiotic stimulusCarbonic anhydrase 9Homo sapiens (human)
response to testosteroneCarbonic anhydrase 9Homo sapiens (human)
secretionCarbonic anhydrase 9Homo sapiens (human)
one-carbon metabolic processCarbonic anhydrase 9Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (10)

Processvia Protein(s)Taxonomy
arylesterase activityCarbonic anhydrase 2Homo sapiens (human)
carbonate dehydratase activityCarbonic anhydrase 2Homo sapiens (human)
protein bindingCarbonic anhydrase 2Homo sapiens (human)
zinc ion bindingCarbonic anhydrase 2Homo sapiens (human)
cyanamide hydratase activityCarbonic anhydrase 2Homo sapiens (human)
steryl-sulfatase activitySteryl-sulfataseHomo sapiens (human)
sulfuric ester hydrolase activitySteryl-sulfataseHomo sapiens (human)
metal ion bindingSteryl-sulfataseHomo sapiens (human)
arylsulfatase activitySteryl-sulfataseHomo sapiens (human)
carbonate dehydratase activityCarbonic anhydrase 9Homo sapiens (human)
protein bindingCarbonic anhydrase 9Homo sapiens (human)
zinc ion bindingCarbonic anhydrase 9Homo sapiens (human)
molecular function activator activityCarbonic anhydrase 9Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (17)

Processvia Protein(s)Taxonomy
cytoplasmCarbonic anhydrase 2Homo sapiens (human)
cytosolCarbonic anhydrase 2Homo sapiens (human)
plasma membraneCarbonic anhydrase 2Homo sapiens (human)
myelin sheathCarbonic anhydrase 2Homo sapiens (human)
apical part of cellCarbonic anhydrase 2Homo sapiens (human)
extracellular exosomeCarbonic anhydrase 2Homo sapiens (human)
cytoplasmCarbonic anhydrase 2Homo sapiens (human)
plasma membraneCarbonic anhydrase 2Homo sapiens (human)
apical part of cellCarbonic anhydrase 2Homo sapiens (human)
lysosomeSteryl-sulfataseHomo sapiens (human)
endosomeSteryl-sulfataseHomo sapiens (human)
endoplasmic reticulumSteryl-sulfataseHomo sapiens (human)
endoplasmic reticulum lumenSteryl-sulfataseHomo sapiens (human)
endoplasmic reticulum membraneSteryl-sulfataseHomo sapiens (human)
Golgi apparatusSteryl-sulfataseHomo sapiens (human)
plasma membraneSteryl-sulfataseHomo sapiens (human)
membraneSteryl-sulfataseHomo sapiens (human)
intracellular membrane-bounded organelleSteryl-sulfataseHomo sapiens (human)
nucleolusCarbonic anhydrase 9Homo sapiens (human)
plasma membraneCarbonic anhydrase 9Homo sapiens (human)
membraneCarbonic anhydrase 9Homo sapiens (human)
basolateral plasma membraneCarbonic anhydrase 9Homo sapiens (human)
microvillus membraneCarbonic anhydrase 9Homo sapiens (human)
plasma membraneCarbonic anhydrase 9Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (44)

Assay IDTitleYearJournalArticle
AID275890Growth inhibition of human DU145 cell line2006Journal of medicinal chemistry, Dec-28, Volume: 49, Issue:26
2-substituted estradiol bis-sulfamates, multitargeted antitumor agents: synthesis, in vitro SAR, protein crystallography, and in vivo activity.
AID473860Inhibition of bovine brain tubulin assembly assessed as decrease in turbidity after 20 mins2010Journal of medicinal chemistry, Apr-08, Volume: 53, Issue:7
Synthesis, antitubulin, and antiproliferative SAR of analogues of 2-methoxyestradiol-3,17-O,O-bis-sulfamate.
AID275897Inhibition of MDA-MB-435 growth xenografted in mouse at 20 mg/kg, po after 28 days2006Journal of medicinal chemistry, Dec-28, Volume: 49, Issue:26
2-substituted estradiol bis-sulfamates, multitargeted antitumor agents: synthesis, in vitro SAR, protein crystallography, and in vivo activity.
AID297661Antitumor activity against human DU145 cells xenografted athymic mouse at 20 mg/kg/day, po after 25 days2007Journal of medicinal chemistry, Sep-06, Volume: 50, Issue:18
3,17-disubstituted 2-alkylestra-1,3,5(10)-trien-3-ol derivatives: synthesis, in vitro and in vivo anticancer activity.
AID1624851Inhibition of carbonic anhydrase 9 (unknown origin) expressed in Escherichia coli BL21 by stopped-flow CO2 hydration assay2019Journal of medicinal chemistry, 02-28, Volume: 62, Issue:4
3,17β-Bis-sulfamoyloxy-2-methoxyestra-1,3,5(10)-triene and Nonsteroidal Sulfamate Derivatives Inhibit Carbonic Anhydrase IX: Structure-Activity Optimization for Isoform Selectivity.
AID275889Growth inhibition of human SN12-C cell line2006Journal of medicinal chemistry, Dec-28, Volume: 49, Issue:26
2-substituted estradiol bis-sulfamates, multitargeted antitumor agents: synthesis, in vitro SAR, protein crystallography, and in vivo activity.
AID1600030Antiproliferative activity against human MDA-MB-231 cells2019European journal of medicinal chemistry, Oct-01, Volume: 179Sulfamates in drug design and discovery: Pre-clinical and clinical investigations.
AID611423Growth inhibition of human SN12C cells2011Journal of medicinal chemistry, Jul-14, Volume: 54, Issue:13
Structure-activity relationships of C-17-substituted estratriene-3-O-sulfamates as anticancer agents.
AID1249520Inhibition of carbonic anhydrase 2 (unknown origin)2015Journal of medicinal chemistry, Oct-08, Volume: 58, Issue:19
Discovery and Development of the Aryl O-Sulfamate Pharmacophore for Oncology and Women's Health.
AID275887Growth inhibition of human UACC62 cell line2006Journal of medicinal chemistry, Dec-28, Volume: 49, Issue:26
2-substituted estradiol bis-sulfamates, multitargeted antitumor agents: synthesis, in vitro SAR, protein crystallography, and in vivo activity.
AID473856Antiproliferative activity against human UACC62 cells after 96 hrs by WST-1 assay2010Journal of medicinal chemistry, Apr-08, Volume: 53, Issue:7
Synthesis, antitubulin, and antiproliferative SAR of analogues of 2-methoxyestradiol-3,17-O,O-bis-sulfamate.
AID611424Growth inhibition of human NCI60 cells2011Journal of medicinal chemistry, Jul-14, Volume: 54, Issue:13
Structure-activity relationships of C-17-substituted estratriene-3-O-sulfamates as anticancer agents.
AID297660Antitumor activity against human DU145 cells xenografted athymic mouse at 10 mg/kg/day, po after 25 days2007Journal of medicinal chemistry, Sep-06, Volume: 50, Issue:18
3,17-disubstituted 2-alkylestra-1,3,5(10)-trien-3-ol derivatives: synthesis, in vitro and in vivo anticancer activity.
AID1600029Antiproliferative activity against human MCF7 cells2019European journal of medicinal chemistry, Oct-01, Volume: 179Sulfamates in drug design and discovery: Pre-clinical and clinical investigations.
AID275888Growth inhibition of human OVCAR-3 cell line2006Journal of medicinal chemistry, Dec-28, Volume: 49, Issue:26
2-substituted estradiol bis-sulfamates, multitargeted antitumor agents: synthesis, in vitro SAR, protein crystallography, and in vivo activity.
AID297654Antiproliferative activity against human MDA-MB-231 cells after 96 hrs by WST1 assay2007Journal of medicinal chemistry, Sep-06, Volume: 50, Issue:18
3,17-disubstituted 2-alkylestra-1,3,5(10)-trien-3-ol derivatives: synthesis, in vitro and in vivo anticancer activity.
AID473852Antiproliferative activity against human MDA-MB-231 cells after 96 hrs by WST-1 assay2010Journal of medicinal chemistry, Apr-08, Volume: 53, Issue:7
Synthesis, antitubulin, and antiproliferative SAR of analogues of 2-methoxyestradiol-3,17-O,O-bis-sulfamate.
AID275891Growth inhibition of human MDA-MB-435 cell line2006Journal of medicinal chemistry, Dec-28, Volume: 49, Issue:26
2-substituted estradiol bis-sulfamates, multitargeted antitumor agents: synthesis, in vitro SAR, protein crystallography, and in vivo activity.
AID473861Displacement of [3H]colchicine from bovine brain tubulin at 5 uM after 10 mins2010Journal of medicinal chemistry, Apr-08, Volume: 53, Issue:7
Synthesis, antitubulin, and antiproliferative SAR of analogues of 2-methoxyestradiol-3,17-O,O-bis-sulfamate.
AID275885Growth inhibition of human HOP62 cell line2006Journal of medicinal chemistry, Dec-28, Volume: 49, Issue:26
2-substituted estradiol bis-sulfamates, multitargeted antitumor agents: synthesis, in vitro SAR, protein crystallography, and in vivo activity.
AID1624852Inhibition of carbonic anhydrase 2 (unknown origin) by stopped-flow CO2 hydration assay2019Journal of medicinal chemistry, 02-28, Volume: 62, Issue:4
3,17β-Bis-sulfamoyloxy-2-methoxyestra-1,3,5(10)-triene and Nonsteroidal Sulfamate Derivatives Inhibit Carbonic Anhydrase IX: Structure-Activity Optimization for Isoform Selectivity.
AID611418Growth inhibition of human HOP62 cells2011Journal of medicinal chemistry, Jul-14, Volume: 54, Issue:13
Structure-activity relationships of C-17-substituted estratriene-3-O-sulfamates as anticancer agents.
AID297657Antitumor activity against human MDA-MB-231 cells xenografted athymic mouse at 60 mg/kg/day, po after 28 days2007Journal of medicinal chemistry, Sep-06, Volume: 50, Issue:18
3,17-disubstituted 2-alkylestra-1,3,5(10)-trien-3-ol derivatives: synthesis, in vitro and in vivo anticancer activity.
AID297658Antitumor activity against human MDA-MB-231 cells xenografted athymic mouse at 90 mg/kg, po thrice a week for 4 weeks2007Journal of medicinal chemistry, Sep-06, Volume: 50, Issue:18
3,17-disubstituted 2-alkylestra-1,3,5(10)-trien-3-ol derivatives: synthesis, in vitro and in vivo anticancer activity.
AID275883Antiproliferative activity against human MCF7 cell line2006Journal of medicinal chemistry, Dec-28, Volume: 49, Issue:26
2-substituted estradiol bis-sulfamates, multitargeted antitumor agents: synthesis, in vitro SAR, protein crystallography, and in vivo activity.
AID473857Antiproliferative activity against human OVCAR-3 cells after 96 hrs by WST-1 assay2010Journal of medicinal chemistry, Apr-08, Volume: 53, Issue:7
Synthesis, antitubulin, and antiproliferative SAR of analogues of 2-methoxyestradiol-3,17-O,O-bis-sulfamate.
AID473855Antiproliferative activity against human SF539 cells after 96 hrs by WST-1 assay2010Journal of medicinal chemistry, Apr-08, Volume: 53, Issue:7
Synthesis, antitubulin, and antiproliferative SAR of analogues of 2-methoxyestradiol-3,17-O,O-bis-sulfamate.
AID275900Antiproliferative activity against human MCF7 cell line at 70 nM2006Journal of medicinal chemistry, Dec-28, Volume: 49, Issue:26
2-substituted estradiol bis-sulfamates, multitargeted antitumor agents: synthesis, in vitro SAR, protein crystallography, and in vivo activity.
AID47745Compound was tested for inhibition of human carbonic anhydrase (hCA II)2003Bioorganic & medicinal chemistry letters, Mar-10, Volume: 13, Issue:5
Docking studies of sulphamate inhibitors of estrone sulphatase in human carbonic anhydrase II.
AID611420Growth inhibition of human SF539 cells2011Journal of medicinal chemistry, Jul-14, Volume: 54, Issue:13
Structure-activity relationships of C-17-substituted estratriene-3-O-sulfamates as anticancer agents.
AID275881Inhibition of STS in placental microsomes by radiometric assay2006Journal of medicinal chemistry, Dec-28, Volume: 49, Issue:26
2-substituted estradiol bis-sulfamates, multitargeted antitumor agents: synthesis, in vitro SAR, protein crystallography, and in vivo activity.
AID275886Growth inhibition of human HCT116 cell line2006Journal of medicinal chemistry, Dec-28, Volume: 49, Issue:26
2-substituted estradiol bis-sulfamates, multitargeted antitumor agents: synthesis, in vitro SAR, protein crystallography, and in vivo activity.
AID611422Growth inhibition of human OVCAR3 cells2011Journal of medicinal chemistry, Jul-14, Volume: 54, Issue:13
Structure-activity relationships of C-17-substituted estratriene-3-O-sulfamates as anticancer agents.
AID473858Antiproliferative activity against human SN12C cells after 96 hrs by WST-1 assay2010Journal of medicinal chemistry, Apr-08, Volume: 53, Issue:7
Synthesis, antitubulin, and antiproliferative SAR of analogues of 2-methoxyestradiol-3,17-O,O-bis-sulfamate.
AID473853Antiproliferative activity against human HOP62 cells after 96 hrs by WST-1 assay2010Journal of medicinal chemistry, Apr-08, Volume: 53, Issue:7
Synthesis, antitubulin, and antiproliferative SAR of analogues of 2-methoxyestradiol-3,17-O,O-bis-sulfamate.
AID473854Antiproliferative activity against human HCT116 cells after 96 hrs by WST-1 assay2010Journal of medicinal chemistry, Apr-08, Volume: 53, Issue:7
Synthesis, antitubulin, and antiproliferative SAR of analogues of 2-methoxyestradiol-3,17-O,O-bis-sulfamate.
AID297659Antitumor activity against human MDA-MB-231 cells xenografted athymic mouse at 200 mg/kg, po, once a week for 4 weeks2007Journal of medicinal chemistry, Sep-06, Volume: 50, Issue:18
3,17-disubstituted 2-alkylestra-1,3,5(10)-trien-3-ol derivatives: synthesis, in vitro and in vivo anticancer activity.
AID297653Antiproliferative activity against human DU145 cells after 96 hrs by WST1 assay2007Journal of medicinal chemistry, Sep-06, Volume: 50, Issue:18
3,17-disubstituted 2-alkylestra-1,3,5(10)-trien-3-ol derivatives: synthesis, in vitro and in vivo anticancer activity.
AID473851Antiproliferative activity against human DU145 cells after 96 hrs by WST-1 assay2010Journal of medicinal chemistry, Apr-08, Volume: 53, Issue:7
Synthesis, antitubulin, and antiproliferative SAR of analogues of 2-methoxyestradiol-3,17-O,O-bis-sulfamate.
AID611421Growth inhibition of human UACC62 cells2011Journal of medicinal chemistry, Jul-14, Volume: 54, Issue:13
Structure-activity relationships of C-17-substituted estratriene-3-O-sulfamates as anticancer agents.
AID1624855Selectivity ratio of Ki for carbonic anhydrase 2 (unknown origin) to Ki for carbonic anhydrase 9 (unknown origin) expressed in Escherichia coli BL212019Journal of medicinal chemistry, 02-28, Volume: 62, Issue:4
3,17β-Bis-sulfamoyloxy-2-methoxyestra-1,3,5(10)-triene and Nonsteroidal Sulfamate Derivatives Inhibit Carbonic Anhydrase IX: Structure-Activity Optimization for Isoform Selectivity.
AID275892Growth inhibition of human SF539 cell line2006Journal of medicinal chemistry, Dec-28, Volume: 49, Issue:26
2-substituted estradiol bis-sulfamates, multitargeted antitumor agents: synthesis, in vitro SAR, protein crystallography, and in vivo activity.
AID297662Antitumor activity against human DU145 cells xenografted athymic mouse at 40 mg/kg/day, po after 25 days2007Journal of medicinal chemistry, Sep-06, Volume: 50, Issue:18
3,17-disubstituted 2-alkylestra-1,3,5(10)-trien-3-ol derivatives: synthesis, in vitro and in vivo anticancer activity.
AID977610Experimentally measured binding affinity data (Ki) for protein-ligand complexes derived from PDB2010Biochemistry, Apr-27, Volume: 49, Issue:16
Structures of human carbonic anhydrase II/inhibitor complexes reveal a second binding site for steroidal and nonsteroidal inhibitors.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (13)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's6 (46.15)29.6817
2010's7 (53.85)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 11.77

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index11.77 (24.57)
Research Supply Index2.64 (2.92)
Research Growth Index4.41 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (11.77)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (7.69%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other12 (92.31%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]